Improvement of antifungal activity and therapeutic profile of fluconazole by its complexation with copper(II) and zinc(II) ions. Complex characterization and antimicrobial activity studies
Authors
Stevanović, NevenaAleksic, Ivana
Kljun, Jakob
Ašanin, Darko
Andrejević, Tina
Nikodinović-Runić, Jasmina
Turel, Iztok
Djuran, Miloš
Glišić, Biljana
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Over the last few decades, invasive fungal infections represent a serious problem for modern-day healthcare. Aspergillus, Candida and Cryptococcus species are the most common pathogens causing life-threatening infections. Therapeutic options for the treatment of fungal infections are presently limited to only four classes of compounds and each of these drug classes has significant therapeutic limitations, including serious toxic-side effects, resistance development and limited routes of administration. In order to overcome resistance of the clinically used antifungal triazole agents, we synthesized zinc(II) and copper(II) complexes with fluconazole (flz), {[ZnCl2(flz)2]·2C2H5OH}n (1) and {[CuCl2(flz)2].5H2O}n (2). These complexes were obtained from the reactions between ZnCl2 or CuCl2·2H2O with this antifungal agent in 1 : 2 molar ratio in ethanol at room temperature. The compounds were characterized by elemental analysis, NMR, IR and UV-Vis spectroscopy and mass spectrometry. The crys...tal structure of complex 1 was determined by a single-crystal X-ray diffraction analysis. The antimicrobial effect of both complexes and fluconazole was evaluated against different Candida species as well as Gram-positive and Gram-negative bacteria by means of minimal inhibitory concentrations (MICs). The obtained results have shown that, in most cases, the coordination of fluconazole to Zn(II) and Cu(II) ions leads to the enhancement of its antifungal activity. Both complexes showed strong inhibitory activity against C. albicans biofilm formation at concentrations lower than MIC values, as well as strong inhibition of C. albicans filamentation.
Source:
Electronic Conference on Medicinal Chemistry, 2020Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200042 (University of Belgrade, Institute of Molecular Genetics and Genetic Engineering) (RS-MESTD-inst-2020-200042)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200122 (University of Kragujevac, Faculty of Science) (RS-MESTD-inst-2020-200122)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200378 (Institute of Information Technology) (RS-MESTD-inst-2020-200378)
- Slovenian Research Agency (grant P1-0175)
- Funding from the Serbian Academy of Sciences and Arts under strategic projects programme - grant agreement No. 01-2019-F65
- project of this institution No. F128.
Note:
- 6th International Electronic Conference on Medicinal Chemistry
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https://sciforum.net/paper/view/7373 - Version of
https://doi.org/10.3390/ECMC2020-07373
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Institut za molekularnu genetiku i genetičko inženjerstvoTY - CONF AU - Stevanović, Nevena AU - Aleksic, Ivana AU - Kljun, Jakob AU - Ašanin, Darko AU - Andrejević, Tina AU - Nikodinović-Runić, Jasmina AU - Turel, Iztok AU - Djuran, Miloš AU - Glišić, Biljana PY - 2020 UR - https://imagine.imgge.bg.ac.rs/handle/123456789/1641 AB - Over the last few decades, invasive fungal infections represent a serious problem for modern-day healthcare. Aspergillus, Candida and Cryptococcus species are the most common pathogens causing life-threatening infections. Therapeutic options for the treatment of fungal infections are presently limited to only four classes of compounds and each of these drug classes has significant therapeutic limitations, including serious toxic-side effects, resistance development and limited routes of administration. In order to overcome resistance of the clinically used antifungal triazole agents, we synthesized zinc(II) and copper(II) complexes with fluconazole (flz), {[ZnCl2(flz)2]·2C2H5OH}n (1) and {[CuCl2(flz)2].5H2O}n (2). These complexes were obtained from the reactions between ZnCl2 or CuCl2·2H2O with this antifungal agent in 1 : 2 molar ratio in ethanol at room temperature. The compounds were characterized by elemental analysis, NMR, IR and UV-Vis spectroscopy and mass spectrometry. The crystal structure of complex 1 was determined by a single-crystal X-ray diffraction analysis. The antimicrobial effect of both complexes and fluconazole was evaluated against different Candida species as well as Gram-positive and Gram-negative bacteria by means of minimal inhibitory concentrations (MICs). The obtained results have shown that, in most cases, the coordination of fluconazole to Zn(II) and Cu(II) ions leads to the enhancement of its antifungal activity. Both complexes showed strong inhibitory activity against C. albicans biofilm formation at concentrations lower than MIC values, as well as strong inhibition of C. albicans filamentation. C3 - Electronic Conference on Medicinal Chemistry T1 - Improvement of antifungal activity and therapeutic profile of fluconazole by its complexation with copper(II) and zinc(II) ions. Complex characterization and antimicrobial activity studies DO - 10.3390/ECMC2020-07373 ER -
@conference{ author = "Stevanović, Nevena and Aleksic, Ivana and Kljun, Jakob and Ašanin, Darko and Andrejević, Tina and Nikodinović-Runić, Jasmina and Turel, Iztok and Djuran, Miloš and Glišić, Biljana", year = "2020", abstract = "Over the last few decades, invasive fungal infections represent a serious problem for modern-day healthcare. Aspergillus, Candida and Cryptococcus species are the most common pathogens causing life-threatening infections. Therapeutic options for the treatment of fungal infections are presently limited to only four classes of compounds and each of these drug classes has significant therapeutic limitations, including serious toxic-side effects, resistance development and limited routes of administration. In order to overcome resistance of the clinically used antifungal triazole agents, we synthesized zinc(II) and copper(II) complexes with fluconazole (flz), {[ZnCl2(flz)2]·2C2H5OH}n (1) and {[CuCl2(flz)2].5H2O}n (2). These complexes were obtained from the reactions between ZnCl2 or CuCl2·2H2O with this antifungal agent in 1 : 2 molar ratio in ethanol at room temperature. The compounds were characterized by elemental analysis, NMR, IR and UV-Vis spectroscopy and mass spectrometry. The crystal structure of complex 1 was determined by a single-crystal X-ray diffraction analysis. The antimicrobial effect of both complexes and fluconazole was evaluated against different Candida species as well as Gram-positive and Gram-negative bacteria by means of minimal inhibitory concentrations (MICs). The obtained results have shown that, in most cases, the coordination of fluconazole to Zn(II) and Cu(II) ions leads to the enhancement of its antifungal activity. Both complexes showed strong inhibitory activity against C. albicans biofilm formation at concentrations lower than MIC values, as well as strong inhibition of C. albicans filamentation.", journal = "Electronic Conference on Medicinal Chemistry", title = "Improvement of antifungal activity and therapeutic profile of fluconazole by its complexation with copper(II) and zinc(II) ions. Complex characterization and antimicrobial activity studies", doi = "10.3390/ECMC2020-07373" }
Stevanović, N., Aleksic, I., Kljun, J., Ašanin, D., Andrejević, T., Nikodinović-Runić, J., Turel, I., Djuran, M.,& Glišić, B.. (2020). Improvement of antifungal activity and therapeutic profile of fluconazole by its complexation with copper(II) and zinc(II) ions. Complex characterization and antimicrobial activity studies. in Electronic Conference on Medicinal Chemistry. https://doi.org/10.3390/ECMC2020-07373
Stevanović N, Aleksic I, Kljun J, Ašanin D, Andrejević T, Nikodinović-Runić J, Turel I, Djuran M, Glišić B. Improvement of antifungal activity and therapeutic profile of fluconazole by its complexation with copper(II) and zinc(II) ions. Complex characterization and antimicrobial activity studies. in Electronic Conference on Medicinal Chemistry. 2020;. doi:10.3390/ECMC2020-07373 .
Stevanović, Nevena, Aleksic, Ivana, Kljun, Jakob, Ašanin, Darko, Andrejević, Tina, Nikodinović-Runić, Jasmina, Turel, Iztok, Djuran, Miloš, Glišić, Biljana, "Improvement of antifungal activity and therapeutic profile of fluconazole by its complexation with copper(II) and zinc(II) ions. Complex characterization and antimicrobial activity studies" in Electronic Conference on Medicinal Chemistry (2020), https://doi.org/10.3390/ECMC2020-07373 . .